Star Collector: Bermuda & Caribbean Island Explorer 

Oct 22, 2027 — Nov 8, 2027

Starting from

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BOSTON, MA → SAN JUAN

17 Nights on Star Pride

Popular Highlights

Map routes may vary by sailing. Actual itineraries are listed below.
1
OCT 22, 2027
Boston
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

2
OCT 23, 2027
AT SEA
3
OCT 24, 2027
AT SEA
4
OCT 25, 2027
Hamilton
ARRIVE
8:45 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

5
OCT 26, 2027
Hamilton
ARRIVE
12:00 AM
DEPART
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

St. George's
ARRIVE
10:00 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

6
OCT 27, 2027
St. George's
ARRIVE
12:00 AM
DEPART
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

7
OCT 28, 2027
AT SEA
8
OCT 29, 2027
AT SEA
9
OCT 30, 2027
Gustavia
ARRIVE
10:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

10
OCT 31, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

11
NOV 01, 2027
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

12
NOV 02, 2027
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$139

St. John, Island tour Featuring Annaberg Ruins

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy
Price
$99

St. John, Lind Point Trail Eco Hike

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$129

St. John, Trunk Bay Snorkeling Experience

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149
13
NOV 03, 2027
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

14
NOV 04, 2027
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

15
NOV 05, 2027
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

16
NOV 06, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

17
NOV 07, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

18
NOV 08, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Star Pride

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests

Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

No other dates are available.

Star Collector: Bermuda & Caribbean Island Explorer 

BOSTON, MA → SAN JUAN

17 Nights on Star Pride

Oct 22, 2027 — Nov 8, 2027

1
OCT 22, 2027
Boston
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

2
OCT 23, 2027
AT SEA
3
OCT 24, 2027
AT SEA
4
OCT 25, 2027
Hamilton
ARRIVE
8:45 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

5
OCT 26, 2027
Hamilton
ARRIVE
12:00 AM
DEPART
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

St. George's
ARRIVE
10:00 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

6
OCT 27, 2027
St. George's
ARRIVE
12:00 AM
DEPART
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

7
OCT 28, 2027
AT SEA
8
OCT 29, 2027
AT SEA
9
OCT 30, 2027
Gustavia
ARRIVE
10:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

10
OCT 31, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

11
NOV 01, 2027
San Juan
ARRIVE
7:00 AM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

12
NOV 02, 2027
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

St. John, Champagne Catamaran Sail

Spend a relaxing self-guided day at Cinnamon Bay Beach, with at least three hours to swim, explore historic ruins, or unwind beneath the palms in complimentary lounge chairs. Enjoy a casual snack lunch and drinks from the beachside snack shack whenever you’re feeling thirsty or hungry.
Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$139 USD

St. John, Island tour Featuring Annaberg Ruins

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$99 USD

St. John, Lind Point Trail Eco Hike

Set out from Cruz Bay with an ecologist guide for a scenic hike through lush tropical forest, learning about local wildlife, native history, and island culture. Take in sweeping views of St. Thomas and the British Virgin Islands before reaching tranquil Honeymoon Beach, where you can swim or relax beneath coconut trees. Continue along the Lind Point trail back to Cruz Bay.
Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$129 USD

St. John, Trunk Bay Snorkeling Experience

St. John is a breathtaking island known for its pristine white-sand beaches and lush tropical landscapes. Enjoy scenic views of Cruz Bay, Hawksnest Bay, and the historic Caneel Bay Plantation as you make your way to the highlight of the tour—iconic Trunk Bay. Here, a unique underwater snorkeling trail awaits. Spend more than 90 minutes swimming and snorkeling along the marked route, where vibrant corals and tropical fish are easy to spot, or simply unwind beneath the shade of a palm tree. Snorkel gear, instruction, and a lounge chair are all included. Please note: Wear a swimsuit and bring a towel, sunscreen, and a hat.
Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149 USD

St. John, Champagne Catamaran Sail

Set sail on a relaxing three-hour catamaran cruise through Virgin Islands National Park, enjoying shaded seating or sun deck views as you head to a vibrant snorkel site. Explore colorful reefs teeming with tropical fish and maybe even a sea turtle, or simply float on the crystal-clear water. Visit secluded Honeymoon Beach (conditions permitting) before unwinding with snacks and drinks on a scenic sail back to St. John.
Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149 USD

13
NOV 03, 2027
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

14
NOV 04, 2027
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

15
NOV 05, 2027
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

16
NOV 06, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

17
NOV 07, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

18
NOV 08, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.